Influencing the binding selectivity of self-assembled cyclodextrin monolayers on gold through their architecture

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Jong de, Menno R. and Huskens, Jurriaan and Reinhoudt, David N. (2001) Influencing the binding selectivity of self-assembled cyclodextrin monolayers on gold through their architecture. Chemistry: a European journal, 7 (19). pp. 4164-4170. ISSN 0947-6539

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Abstract:Cyclodextrin derivatives modified with seven thioether moieties (1) or with one thiol moiety (2) bind to gold. Monolayers on gold of 1 or mixed monolayers of 2 and mercaptoundecanol were characterized by electrochemistry, wettability, and atomic force microscopy (AFM). Monolayers of 1 are well-ordered, but the order in the mixed monolayers depends on the ratio of 2 to mercaptoundecanol. With sufficient alkyl chains to fill the space under the cyclodextrin moiety of 2, the monolayers are densely packed. Guest recognition at these monolayers in water was studied by surface plasmon resonance (SPR) spectroscopy. For simple organic guests, monolayers of 1 showed the same selectivity and binding strength as -cyclodextrin in solution; however, the selectivity towards steroidal bile salts differs from solution. The mixed monolayers of 2, in which the cyclodextrin is less substituted and has more flexibility, bind steroidal guests (6 a-6 e) with the same selectivity as -cyclodextrin in solution.
Item Type:Article
Copyright:© 2001 WILEY-VCH Verlag
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/36750
Official URL:http://dx.doi.org/10.1002/1521-3765(20011001)7:19<4164::AID-CHEM4164>3.0.CO;2-Q
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